1340592-97-3Relevant academic research and scientific papers
Catalyst-Controlled Regioselectivity in Pd-Catalyzed Aerobic Oxidative Arylation of Indoles
Wang, Dian,Salazar, Chase A.,Stahl, Shannon S.
, p. 2198 - 2203 (2021)
Pd-catalyzed C-H arylation of heteroarenes is an important and widely studied synthetic transformation; however, the regioselectivity is often substrate-controlled. Here, we report catalyst-controlled regioselectivity in the Pd-catalyzed oxidative coupling ofN-(phenylsulfonyl)indoles and aryl boronic acids using O2as the oxidant. Both C2- and C3-arylated indoles are obtained in good yield with >10:1 selectivity. A switch from C2 to C3 regioselectivity is achieved by adding 4,5-diazafluoren-9-one or 2,2′-bipyrimidine as an ancillary ligand to a “ligand-free” Pd(OTs)2catalyst system. Density functional theory calculations indicate that the switch in selectivity arises from a change in the mechanism, from a C2-selective oxidative-Heck pathway to a C3-selective C-H activation/reductive elimination pathway.
Synthesis and pharmacological evaluation of indole-based sigma receptor ligands
Mésangeau, Christophe,Amata, Emanuele,Alsharif, Walid,Seminerio, Michael J.,Robson, Matthew J.,Matsumoto, Rae R.,Poupaert, Jacques H.,McCurdy, Christopher R.
experimental part, p. 5154 - 5161 (2011/11/29)
A series of novel indole-based analogs were prepared and their affinities for sigma receptors were determined using in vitro radioligand binding assays. The results of this study identified several compounds with nanomolar sigma-2 affinity and significant
